TW200914013A - Antiviral compounds - Google Patents
Antiviral compounds Download PDFInfo
- Publication number
- TW200914013A TW200914013A TW097123925A TW97123925A TW200914013A TW 200914013 A TW200914013 A TW 200914013A TW 097123925 A TW097123925 A TW 097123925A TW 97123925 A TW97123925 A TW 97123925A TW 200914013 A TW200914013 A TW 200914013A
- Authority
- TW
- Taiwan
- Prior art keywords
- group
- alkyl
- compound
- alkoxy
- alkynyl
- Prior art date
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 295
- 230000000840 anti-viral effect Effects 0.000 title abstract description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 279
- -1 -OH Chemical group 0.000 claims description 272
- 125000003342 alkenyl group Chemical group 0.000 claims description 182
- 125000000304 alkynyl group Chemical group 0.000 claims description 182
- OAKJQQAXSVQMHS-UHFFFAOYSA-N hydrazine group Chemical group NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 177
- 125000003118 aryl group Chemical group 0.000 claims description 134
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 125
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 124
- 125000005843 halogen group Chemical group 0.000 claims description 119
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 112
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 103
- 125000003545 alkoxy group Chemical group 0.000 claims description 100
- 125000000027 (C1-C10) alkoxy group Chemical group 0.000 claims description 96
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 96
- 125000000623 heterocyclic group Chemical group 0.000 claims description 96
- 125000001072 heteroaryl group Chemical group 0.000 claims description 93
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 81
- 125000004432 carbon atom Chemical group C* 0.000 claims description 69
- 125000002252 acyl group Chemical group 0.000 claims description 67
- 125000004122 cyclic group Chemical group 0.000 claims description 67
- 229910052717 sulfur Inorganic materials 0.000 claims description 67
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 61
- 229910052736 halogen Inorganic materials 0.000 claims description 53
- 239000003112 inhibitor Substances 0.000 claims description 52
- 150000003839 salts Chemical class 0.000 claims description 52
- 125000004423 acyloxy group Chemical group 0.000 claims description 48
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 48
- 150000002367 halogens Chemical class 0.000 claims description 45
- 229910052757 nitrogen Inorganic materials 0.000 claims description 43
- 125000001188 haloalkyl group Chemical group 0.000 claims description 42
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 37
- 238000011282 treatment Methods 0.000 claims description 36
- 229910052731 fluorine Inorganic materials 0.000 claims description 35
- 239000000651 prodrug Substances 0.000 claims description 35
- 229940002612 prodrug Drugs 0.000 claims description 35
- 229910052794 bromium Inorganic materials 0.000 claims description 34
- 229910052801 chlorine Inorganic materials 0.000 claims description 30
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 30
- 239000003814 drug Substances 0.000 claims description 29
- 125000004429 atom Chemical group 0.000 claims description 28
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 28
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 claims description 27
- 150000001412 amines Chemical class 0.000 claims description 26
- 229910052740 iodine Inorganic materials 0.000 claims description 25
- 239000008194 pharmaceutical composition Substances 0.000 claims description 25
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 23
- 125000001424 substituent group Chemical group 0.000 claims description 23
- 229910052739 hydrogen Inorganic materials 0.000 claims description 22
- 239000011593 sulfur Substances 0.000 claims description 21
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 20
- 229940079593 drug Drugs 0.000 claims description 20
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 20
- 239000002243 precursor Substances 0.000 claims description 20
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 19
- 229910052799 carbon Inorganic materials 0.000 claims description 19
- 239000000126 substance Substances 0.000 claims description 19
- 150000001335 aliphatic alkanes Chemical class 0.000 claims description 18
- 125000005110 aryl thio group Chemical group 0.000 claims description 18
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 18
- 125000005842 heteroatom Chemical group 0.000 claims description 18
- 239000002777 nucleoside Substances 0.000 claims description 18
- 229940079322 interferon Drugs 0.000 claims description 17
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims description 17
- 238000002360 preparation method Methods 0.000 claims description 17
- 108010050904 Interferons Proteins 0.000 claims description 16
- 102000014150 Interferons Human genes 0.000 claims description 16
- 108010022999 Serine Proteases Proteins 0.000 claims description 15
- 102000012479 Serine Proteases Human genes 0.000 claims description 15
- 125000004104 aryloxy group Chemical group 0.000 claims description 15
- CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 claims description 14
- IWUCXVSUMQZMFG-AFCXAGJDSA-N Ribavirin Chemical class N1=C(C(=O)N)N=CN1[C@H]1[C@H](O)[C@H](O)[C@@H](CO)O1 IWUCXVSUMQZMFG-AFCXAGJDSA-N 0.000 claims description 14
- 125000004657 aryl sulfonyl amino group Chemical group 0.000 claims description 14
- 239000003795 chemical substances by application Substances 0.000 claims description 14
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 14
- 150000003833 nucleoside derivatives Chemical class 0.000 claims description 14
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 14
- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims description 13
- GSPFUBNBRPVALJ-VIEAGMIOSA-N PR-toxin Chemical compound C1([C@@H]2O[C@@H]2[C@H](OC(C)=O)[C@@H]([C@]1(C1)C)C)=CC(=O)[C@]21O[C@]2(C)C=O GSPFUBNBRPVALJ-VIEAGMIOSA-N 0.000 claims description 13
- 125000003277 amino group Chemical group 0.000 claims description 13
- 125000000468 ketone group Chemical group 0.000 claims description 13
- 125000004656 alkyl sulfonylamino group Chemical group 0.000 claims description 12
- 229940024606 amino acid Drugs 0.000 claims description 12
- 150000001413 amino acids Chemical class 0.000 claims description 12
- 125000002837 carbocyclic group Chemical group 0.000 claims description 12
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 12
- 230000003993 interaction Effects 0.000 claims description 12
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 12
- 238000006467 substitution reaction Methods 0.000 claims description 12
- 239000000725 suspension Substances 0.000 claims description 12
- 201000010099 disease Diseases 0.000 claims description 11
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 11
- RMBPEFMHABBEKP-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2C3=C[CH]C=CC3=CC2=C1 RMBPEFMHABBEKP-UHFFFAOYSA-N 0.000 claims description 11
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 claims description 11
- 125000003396 thiol group Chemical group [H]S* 0.000 claims description 11
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 10
- 125000005119 alkyl cycloalkyl group Chemical group 0.000 claims description 10
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 10
- 125000004414 alkyl thio group Chemical group 0.000 claims description 9
- 229910052760 oxygen Inorganic materials 0.000 claims description 9
- 229940124597 therapeutic agent Drugs 0.000 claims description 9
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 claims description 8
- 125000004422 alkyl sulphonamide group Chemical group 0.000 claims description 8
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 8
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 8
- 239000001257 hydrogen Substances 0.000 claims description 8
- 150000002923 oximes Chemical class 0.000 claims description 8
- 239000000137 peptide hydrolase inhibitor Substances 0.000 claims description 8
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 8
- 229910052707 ruthenium Inorganic materials 0.000 claims description 8
- 125000004778 2,2-difluoroethyl group Chemical group [H]C([H])(*)C([H])(F)F 0.000 claims description 7
- 125000002373 5 membered heterocyclic group Chemical group 0.000 claims description 7
- 125000004070 6 membered heterocyclic group Chemical group 0.000 claims description 7
- 208000005176 Hepatitis C Diseases 0.000 claims description 7
- 125000004421 aryl sulphonamide group Chemical group 0.000 claims description 7
- 125000000962 organic group Chemical group 0.000 claims description 7
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 7
- 125000005037 alkyl phenyl group Chemical group 0.000 claims description 6
- 229940009098 aspartate Drugs 0.000 claims description 6
- 125000002619 bicyclic group Chemical group 0.000 claims description 6
- 125000002757 morpholinyl group Chemical group 0.000 claims description 6
- 229910052762 osmium Inorganic materials 0.000 claims description 6
- SYQBFIAQOQZEGI-UHFFFAOYSA-N osmium atom Chemical compound [Os] SYQBFIAQOQZEGI-UHFFFAOYSA-N 0.000 claims description 6
- 150000004032 porphyrins Chemical class 0.000 claims description 6
- 229910052705 radium Inorganic materials 0.000 claims description 6
- 229910052701 rubidium Inorganic materials 0.000 claims description 6
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 5
- IWUCXVSUMQZMFG-RGDLXGNYSA-N 1-[(2s,3s,4r,5s)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,2,4-triazole-3-carboxamide Chemical compound N1=C(C(=O)N)N=CN1[C@@H]1[C@@H](O)[C@@H](O)[C@H](CO)O1 IWUCXVSUMQZMFG-RGDLXGNYSA-N 0.000 claims description 5
- 239000004475 Arginine Substances 0.000 claims description 5
- OUYCCCASQSFEME-QMMMGPOBSA-N L-tyrosine Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-QMMMGPOBSA-N 0.000 claims description 5
- 125000005213 alkyl heteroaryl group Chemical group 0.000 claims description 5
- ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 claims description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 5
- 239000003937 drug carrier Substances 0.000 claims description 5
- 238000000605 extraction Methods 0.000 claims description 5
- 229950003954 isatoribine Drugs 0.000 claims description 5
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 5
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 5
- 239000001301 oxygen Substances 0.000 claims description 5
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 5
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims description 4
- 101001023866 Arabidopsis thaliana Mannosyl-oligosaccharide glucosidase GCS1 Proteins 0.000 claims description 4
- 229940124158 Protease/peptidase inhibitor Drugs 0.000 claims description 4
- 101800001838 Serine protease/helicase NS3 Proteins 0.000 claims description 4
- 150000001336 alkenes Chemical class 0.000 claims description 4
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 4
- 125000001475 halogen functional group Chemical group 0.000 claims description 4
- HNDVDQJCIGZPNO-UHFFFAOYSA-N histidine Natural products OC(=O)C(N)CC1=CN=CN1 HNDVDQJCIGZPNO-UHFFFAOYSA-N 0.000 claims description 4
- 150000002466 imines Chemical class 0.000 claims description 4
- DMEKUKDWAIXWSL-UHFFFAOYSA-N n,n-dimethyl-7-nitro-9h-fluoren-2-amine Chemical compound [O-][N+](=O)C1=CC=C2C3=CC=C(N(C)C)C=C3CC2=C1 DMEKUKDWAIXWSL-UHFFFAOYSA-N 0.000 claims description 4
- NHKZSTHOYNWEEZ-AFCXAGJDSA-N taribavirin Chemical compound N1=C(C(=N)N)N=CN1[C@H]1[C@H](O)[C@H](O)[C@@H](CO)O1 NHKZSTHOYNWEEZ-AFCXAGJDSA-N 0.000 claims description 4
- 229950006081 taribavirin Drugs 0.000 claims description 4
- OUYCCCASQSFEME-UHFFFAOYSA-N tyrosine Natural products OC(=O)C(N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-UHFFFAOYSA-N 0.000 claims description 4
- 229920002554 vinyl polymer Polymers 0.000 claims description 4
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 3
- 125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 claims description 3
- 125000004777 2-fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 claims description 3
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims description 3
- BPPVUXSMLBXYGG-UHFFFAOYSA-N 4-[3-(4,5-dihydro-1,2-oxazol-3-yl)-2-methyl-4-methylsulfonylbenzoyl]-2-methyl-1h-pyrazol-3-one Chemical compound CC1=C(C(=O)C=2C(N(C)NC=2)=O)C=CC(S(C)(=O)=O)=C1C1=NOCC1 BPPVUXSMLBXYGG-UHFFFAOYSA-N 0.000 claims description 3
- 241001091551 Clio Species 0.000 claims description 3
- ONIBWKKTOPOVIA-BYPYZUCNSA-N L-Proline Chemical compound OC(=O)[C@@H]1CCCN1 ONIBWKKTOPOVIA-BYPYZUCNSA-N 0.000 claims description 3
- 241001465754 Metazoa Species 0.000 claims description 3
- ONIBWKKTOPOVIA-UHFFFAOYSA-N Proline Natural products OC(=O)C1CCCN1 ONIBWKKTOPOVIA-UHFFFAOYSA-N 0.000 claims description 3
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 3
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 3
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 3
- 125000006431 methyl cyclopropyl group Chemical group 0.000 claims description 3
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 3
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 3
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 3
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 3
- CRCTZWNJRMZUIO-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoropropane Chemical group FC(F)(F)[CH]C(F)(F)F CRCTZWNJRMZUIO-UHFFFAOYSA-N 0.000 claims description 2
- 125000006432 1-methyl cyclopropyl group Chemical group [H]C([H])([H])C1(*)C([H])([H])C1([H])[H] 0.000 claims description 2
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 claims description 2
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 2
- FWKQNCXZGNBPFD-UHFFFAOYSA-N Guaiazulene Chemical compound CC(C)C1=CC=C(C)C2=CC=C(C)C2=C1 FWKQNCXZGNBPFD-UHFFFAOYSA-N 0.000 claims description 2
- 101000577106 Mus musculus Mannosyl-oligosaccharide glucosidase Proteins 0.000 claims description 2
- 229940123066 Polymerase inhibitor Drugs 0.000 claims description 2
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical group OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 claims description 2
- 125000004171 alkoxy aryl group Chemical group 0.000 claims description 2
- 125000005928 isopropyloxycarbonyl group Chemical group [H]C([H])([H])C([H])(OC(*)=O)C([H])([H])[H] 0.000 claims description 2
- REOJLIXKJWXUGB-UHFFFAOYSA-N mofebutazone Chemical group O=C1C(CCCC)C(=O)NN1C1=CC=CC=C1 REOJLIXKJWXUGB-UHFFFAOYSA-N 0.000 claims description 2
- ZNPKAOCQMDJBIK-UHFFFAOYSA-N nitrocyanamide Chemical compound [O-][N+](=O)NC#N ZNPKAOCQMDJBIK-UHFFFAOYSA-N 0.000 claims description 2
- 125000005740 oxycarbonyl group Chemical group [*:1]OC([*:2])=O 0.000 claims description 2
- 150000004060 quinone imines Chemical class 0.000 claims description 2
- 229960000329 ribavirin Drugs 0.000 claims description 2
- HZCAHMRRMINHDJ-DBRKOABJSA-N ribavirin Natural products O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1N1N=CN=C1 HZCAHMRRMINHDJ-DBRKOABJSA-N 0.000 claims description 2
- 125000000565 sulfonamide group Chemical group 0.000 claims description 2
- CYFJIBWZIQDUSZ-UHFFFAOYSA-N thioglycine Chemical group NCC(S)=O CYFJIBWZIQDUSZ-UHFFFAOYSA-N 0.000 claims description 2
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims 3
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 2
- CRSOQBOWXPBRES-UHFFFAOYSA-N neopentane Chemical compound CC(C)(C)C CRSOQBOWXPBRES-UHFFFAOYSA-N 0.000 claims 2
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 claims 2
- 125000006433 1-ethyl cyclopropyl group Chemical group [H]C([H])([H])C([H])([H])C1(*)C([H])([H])C1([H])[H] 0.000 claims 1
- RMZNXRYIFGTWPF-UHFFFAOYSA-N 2-nitrosoacetic acid Chemical compound OC(=O)CN=O RMZNXRYIFGTWPF-UHFFFAOYSA-N 0.000 claims 1
- TZYVRXZQAWPIAB-FCLHUMLKSA-N 5-amino-3-[(2r,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-4h-[1,3]thiazolo[4,5-d]pyrimidine-2,7-dione Chemical compound O=C1SC=2C(=O)NC(N)=NC=2N1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O TZYVRXZQAWPIAB-FCLHUMLKSA-N 0.000 claims 1
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 claims 1
- 206010061218 Inflammation Diseases 0.000 claims 1
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- 230000004054 inflammatory process Effects 0.000 claims 1
- JXDYKVIHCLTXOP-UHFFFAOYSA-N isatin Chemical compound C1=CC=C2C(=O)C(=O)NC2=C1 JXDYKVIHCLTXOP-UHFFFAOYSA-N 0.000 claims 1
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims 1
- 235000013536 miso Nutrition 0.000 claims 1
- 229910052703 rhodium Inorganic materials 0.000 claims 1
- 125000001493 tyrosinyl group Chemical group [H]OC1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])(N([H])[H])C(*)=O 0.000 claims 1
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- 238000006243 chemical reaction Methods 0.000 description 101
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- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 52
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- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 48
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- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 44
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- 238000003756 stirring Methods 0.000 description 43
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 42
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- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 38
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- 239000002585 base Substances 0.000 description 32
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- 238000005481 NMR spectroscopy Methods 0.000 description 30
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 29
- GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 28
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 28
- 229910052938 sodium sulfate Inorganic materials 0.000 description 28
- 235000011152 sodium sulphate Nutrition 0.000 description 28
- 230000015572 biosynthetic process Effects 0.000 description 27
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 27
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- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 24
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- OJCSPXHYDFONPU-UHFFFAOYSA-N etoac etoac Chemical compound CCOC(C)=O.CCOC(C)=O OJCSPXHYDFONPU-UHFFFAOYSA-N 0.000 description 21
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- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 20
- 125000006239 protecting group Chemical group 0.000 description 19
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
- C07K5/08—Tripeptides
- C07K5/0802—Tripeptides with the first amino acid being neutral
- C07K5/0804—Tripeptides with the first amino acid being neutral and aliphatic
- C07K5/0808—Tripeptides with the first amino acid being neutral and aliphatic the side chain containing 2 to 4 carbon atoms, e.g. Val, Ile, Leu
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/16—Drugs for disorders of the alimentary tract or the digestive system for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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-
2008
- 2008-06-26 AP AP2009005073A patent/AP2009005073A0/en unknown
- 2008-06-26 JP JP2010514802A patent/JP5465667B2/ja not_active Expired - Fee Related
- 2008-06-26 EA EA200971074A patent/EA200971074A1/ru unknown
- 2008-06-26 CN CN200880104330A patent/CN101801925A/zh active Pending
- 2008-06-26 BR BRPI0813733-1A patent/BRPI0813733A2/pt not_active IP Right Cessation
- 2008-06-26 SG SG2012048484A patent/SG182979A1/en unknown
- 2008-06-26 AU AU2008271117A patent/AU2008271117B2/en not_active Ceased
- 2008-06-26 TW TW097123925A patent/TW200914013A/zh unknown
- 2008-06-26 KR KR1020107002261A patent/KR20100038417A/ko not_active Ceased
- 2008-06-26 WO PCT/US2008/007928 patent/WO2009005677A2/en not_active Ceased
- 2008-06-26 AR ARP080102758A patent/AR068794A1/es not_active Application Discontinuation
- 2008-06-26 MX MX2009013830A patent/MX2009013830A/es not_active Application Discontinuation
- 2008-06-26 EP EP08779772A patent/EP2162432A2/en not_active Withdrawn
- 2008-06-26 US US12/215,601 patent/US8513186B2/en active Active
- 2008-06-26 CA CA2692145A patent/CA2692145C/en not_active Expired - Fee Related
-
2009
- 2009-12-09 IL IL202623A patent/IL202623A0/en unknown
- 2009-12-18 CO CO09145303A patent/CO6251241A2/es not_active Application Discontinuation
-
2010
- 2010-01-27 ZA ZA2010/00614A patent/ZA201000614B/en unknown
- 2010-01-28 EC EC2010009906A patent/ECSP109906A/es unknown
-
2013
- 2013-06-13 JP JP2013124380A patent/JP2013177452A/ja not_active Withdrawn
- 2013-07-01 US US13/932,945 patent/US8809267B2/en active Active
Also Published As
| Publication number | Publication date |
|---|---|
| AU2008271117B2 (en) | 2013-10-24 |
| SG182979A1 (en) | 2012-08-30 |
| CO6251241A2 (es) | 2011-02-21 |
| CA2692145C (en) | 2015-03-03 |
| WO2009005677A2 (en) | 2009-01-08 |
| BRPI0813733A2 (pt) | 2019-11-05 |
| EA200971074A1 (ru) | 2010-08-30 |
| JP5465667B2 (ja) | 2014-04-09 |
| IL202623A0 (en) | 2010-06-30 |
| EP2162432A2 (en) | 2010-03-17 |
| CN101801925A (zh) | 2010-08-11 |
| US8513186B2 (en) | 2013-08-20 |
| MX2009013830A (es) | 2010-03-01 |
| WO2009005677A3 (en) | 2009-03-05 |
| US8809267B2 (en) | 2014-08-19 |
| JP2010532352A (ja) | 2010-10-07 |
| AP2009005073A0 (en) | 2009-12-31 |
| ECSP109906A (es) | 2010-03-31 |
| US20090186869A1 (en) | 2009-07-23 |
| US20140051626A1 (en) | 2014-02-20 |
| AU2008271117A1 (en) | 2009-01-08 |
| CA2692145A1 (en) | 2009-01-08 |
| KR20100038417A (ko) | 2010-04-14 |
| ZA201000614B (en) | 2011-11-30 |
| AR068794A1 (es) | 2009-12-09 |
| JP2013177452A (ja) | 2013-09-09 |
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